Cranberry, Apple & Sausage Stuffed Acorn Squash

Prep Time: 20 minutes | Cook Time: 45 minutes | Serves: 3
Author: Olivelle (styled + Chivillafied by Chivilla Bay)

If cozy had a flavor, this would be it.

This Cranberry, Apple & Sausage Stuffed Acorn Squash is everything we love about fall cooking—warm, hearty, a little sweet, a little savory, and completely comforting. Roasted acorn squash gets filled with savory sausage, tart cranberries, crisp apples, and rosemary, then finished with a drizzle of fig balsamic that ties it all together like magic.

It’s rustic enough for a weeknight dinner but impressive enough for guests. Basically, it’s the kind of meal that makes you want to light a candle, pour a drink, and slow things down a bit.

🛒 Ingredients

For the Acorn Squash

• 3 acorn squash

• 3 tbsp Wild Mushroom & Sage Infused Olive Oil

• 1½ tsp Smokey Bacon Infused Sea Salt

For the Filling

• 1 lb ground sausage

• 1 small red onion, finely diced

• 2 stalks celery, finely diced

• ½ Honeycrisp or Pink Lady apple, finely diced

• ½ cup dried cranberries

• 2 tsp Mediterranean Rosemary Rub & Seasoning

• 1 tsp Smokey Bacon Infused Sea Salt

• 3 tbsp Harvest Fig Barrel Aged Balsamic, divided

🍽️ Directions

1️⃣ Roast the Squash

Preheat oven to 425°F.

Cut about 1 inch off the top of each acorn squash. Scoop out the seeds and place squash on a parchment-lined baking sheet.

Drizzle with Wild Mushroom & Sage Infused Olive Oil and sprinkle with Smokey Bacon Infused Sea Salt. Place cut side down and bake for 30 minutes, or until fork-tender.

2️⃣ Make the Filling

While the squash roasts, heat a skillet over medium heat.

Add sausage, red onion, celery, apple, cranberries, rosemary seasoning, and Smokey Bacon Sea Salt. Cook until sausage is browned and crumbly and the mixture is well combined.

Stir in 2 tbsp Harvest Fig Barrel Aged Balsamic and cook for 1 more minute.

3️⃣ Stuff & Broil

Switch oven to Broil and remove squash from oven.

Flip squash upright and generously stuff with the sausage mixture. Return to oven and broil for 5–8 minutes, until golden on top.

4️⃣ Finish & Serve

Drizzle with remaining 1 tbsp Harvest Fig Barrel Aged Balsamic and serve warm.

💡 Chivilla Bay Tips & Tricks

• Make it meal-prep friendly: The filling can be made a day ahead.

• Want extra crunch? Sprinkle chopped pecans or walnuts on top before broiling.

• No sausage? Ground turkey works great—just season generously.

• Hosting hack: Serve with a simple green salad and crusty bread for an easy, impressive dinner.

This is one of those recipes that feels like fall—comforting, flavorful, and just a little fancy without being fussy. Perfect for cool nights, casual gatherings, or when you want dinner to feel like a hug.